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1 See also  





2 References  














Threose






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From Wikipedia, the free encyclopedia
 


Threose[1]

D-Threose


L-Threose

Names
IUPAC names

D-Threose
L-Threose [2]

Systematic IUPAC name

(2S,3R)-2,3,4-Trihydroxybutanal (D)
(2R,3S)-2,3,4-Trihydroxybutanal (L)

Other names

Threotetrose

Identifiers

CAS Number

  • 95-44-3 (L) checkY
  • 3D model (JSmol)

  • (L): Interactive image
  • ChEBI
    ChemSpider
    ECHA InfoCard 100.002.199 Edit this at Wikidata

    PubChem CID

    UNII
  • MHH79K1BVR (L) checkY
  • CompTox Dashboard (EPA)

    • InChI=1S/C4H8O4/c5-1-3(7)4(8)2-6/h1,3-4,6-8H,2H2/t3-,4-/m1/s1 checkY

      Key: YTBSYETUWUMLBZ-QWWZWVQMSA-N checkY

    • InChI=1/C4H8O4/c5-1-3(7)4(8)2-6/h1,3-4,6-8H,2H2/t3-,4-/m1/s1

      Key: YTBSYETUWUMLBZ-QWWZWVQMBY

    • (D): O=C[C@@H](O)[C@H](O)CO

    • (L): OC[C@H](O)[C@@H](O)C=O

    Properties

    Chemical formula

    C4H8O4
    Molar mass 120.104 g·mol−1
    Appearance Syrup

    Solubility in water

    Very soluble

    Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

    ☒N verify (what is checkY☒N ?)

    Infobox references

    Threose is a four-carbon monosaccharide with molecular formulaC4H8O4. It has a terminal aldehyde group rather than a ketone in its linear chain, and so is considered part of the aldose family of monosaccharides. The threose name can be used to refer to both the D- and L-stereoisomers, and more generally to the racemic mixture (D/L-, equal parts D- and L-) as well as to the more generic threose structure (absolute stereochemistry unspecified).

    The prefix "threo" which derives from threose (and "erythro" from a corresponding diastereomer erythrose) offer a useful way to describe general organic structures with adjacent chiral centers, where "the prefixes... designate the relative configuration of the centers".[3] As is depicted in a Fischer projectionofD-threose, the adjacent substituents will have a syn orientation in the isomer referred to as "threo", and are anti in the isomer referred to as "erythro".[3][4]

    Fischer projections depicting the two enantiomers of threose

    See also[edit]

    References[edit]

    1. ^ Merck Index, 11th Edition, 9317
  • ^ https://iupac.qmul.ac.uk/2carb
  • ^ a b Formulas Using Other Configurational Notations, W. Rausch, accessed 1 March 2011
  • ^ Prof. Rausch helpfully notes that the prefixes "may be applied to racemic compounds, as well as pure enantiomers and meso compounds", and that when depicted in the common "zig-zag" representation, adjacent "substituents may lie on the same side of the carbon chain... [syn] or on opposite sides... [anti]", which is opposite of their depiction in a Fischer projection.

  • Retrieved from "https://en.wikipedia.org/w/index.php?title=Threose&oldid=1175496611"

    Category: 
    Aldotetroses
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